


W is where the wily woman walks

by SuperWoman0124



Series: ABC's of Kinky Sex- Dean/Sam [7]
Category: Supernatural
Genre: Anal Sex, Bottom Sam, Crossdressing, M/M, Masturbation, Slutty! Dean, Slutty!Sam, Top Dean, no prep, slight het
Language: English
Status: Completed
Published: 2015-04-26
Updated: 2015-04-26
Packaged: 2018-03-25 21:14:05
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,164
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3825274
Author URL: https://archiveofourown.org/users/SuperWoman0124/pseuds/SuperWoman0124
Summary: <blockquote class="userstuff">
              <p>Dean Winchester walks into a Victoria Secret with his own little secret. and it's not for any lady. </p><p>Sam catches Dean pursuing one of his kinks. [Dirty Sex included]</p>
            </blockquote>





	W is where the wily woman walks

**Author's Note:**

> I imagine this taking place maybe season 5 or 6, when the boys were still on the road.

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This wasn't the first time the oldest Wincester had walked out of Victoria's Secret cherry-red faced. Even though he knew he'd never see those women again, never have to face them, it was still embarrassing to go in and look for ladies panties in a man's size. 

Rhonda Hurley ruined him forever. The second she took those silk pink panties off her thin calves and offered them to a young, unexperienced, teenage Dean, he knew he'd been in for it. The tight elastic snapped around his waist and his cheeks were as pink as the panties. but it felt pretty good. The smooth silk running up his newly manscaped balls, the tight cord touching all the virgin spots up his ass, into his crack and when he turned to look in the mirror... 

He was drifting off. 

Well, ever since then, he'd give himself this. Not all the time. Just.. every once in awhile. Dean would go out, buy a new pair and wear them around the hotel room. Not on hunts or anything, yuck, but around the hotel? Oh yeah. And damn, did he look good. 

White lace boy shorts had been the way to go. Dean wasn't a thong fan, but these were perfect. He thought they would be scratchy, but eventually, they became quite comfortable, almost forgetting he was wearing them entirely. Sam had left, god knows where for god knows how long, so he slipped on his blue tube top and laid back on the bed. Entirely comfortable, he flipped on the adult channel. He slipped his fingers between the soft lace and his bronzed supple hip, feeding them into the fine coarse pubic hair. He found his interested cock perked up at the touch, throbbing hard and ready, just like he is every time he does this. 

He heard the woman on the screen moan as '70's Pornstache licked her pussy. Dean grasped the base of his cock and ran it to the tip, dipping back down again to spread the pre-come. He fisted his other fingers into his unkempt hair, squeezing gently before letting out a puff of hot breath. He lowered his hand, dragging it delicately down his body, fingertips tickling his abs until he reached the waistband of the beautiful lace and dove in. The lace was tightly pulling on his balls, up his crack and it felt wonderful. He spread his legs and looked at himself in the mirror. Shame over came him, but that didn't stop him. He massaged his balls, softly tugging on them while he fisted his cock, becoming slicker every moment. Dean was so.. so close. He began to twist his fingers when he reached the aching head and the calloused pads of his fingers rubbed the bundle of nerves at the tip. Dean bit down on his plump lower lip as he came, stifling any noises that wanted to escape his throat. 

Everything went black. 

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"...The fuck, man?" 

Dean woke to Sam dropping a paper bag full of eggs and celery, opening his eyes wide and rubbing them with his fingertips, yawning wide and running his hands down his chest to... 

Shit. 

Shit! 

Dean scrambled, covering himself with the thin comforter and watching Sam's face transform from shock to utter terror. 

"Gahd, dude!" Sam covered his eyes with the back of his hand. "Really? Like, really? In **my** bed?" Sam bent at the knees to pick up the remnants of the eggs, sliding three broken shells back into the carton. 

"D-Don't look, Sammy! J-just don't!" Dean wrapped the comforter around himself and ran to the bathroom, ass swaying, cotton lace up his crack where he forgot to cover himself. 

Sam laughed it off. Ha! Dean and his kinks. He padded to the kitchen and began to put the groceries away. As he pulled out the celery, his mind began to wander. Dean's ass looked pretty good in white panties. 

Oh my god. Did he just say that? 

Yeah, he did. Apparently his cock noticed, too. 

He readjusted himself in his suddenly too tight pants, moving his dick to the right side. He squatted, trying to hide it the best way he could, the same way he'd done all these years. It'll go away eventually. After he stops thinking about what Dean did in his bed. Probably jerked off in those underwear. 

That shouldn't be as hot at it was. 

Stop it, Sam. 

Same thing he'd told himself for years. 

Sam put the rest of the groceries away and toed off his battered boots, moving to Dean's bed. Sam stretched his large frame out, hands above his head as he watched the porn that had been left playing. 

He heard a calmness in the bathroom, the shower head giving a steady hiss as Dean probably finished his business. 

Sam peered down to his fully erect cock and gave a sigh. He readjusted once again, it becoming strangely uncomfortable. Sam's hand felt so good through the thin fabric of his jeans and he grasped himself at the base, stopping the moan from emerging from his mouth. He couldn't stop thinking about Dean's ass in the thin white panties and wondered what his cock would look like sheathed in the silk fabric. Sam's mouth dropped wide as he felt a bead of precome leaking from the slit. 

Dean burst through the door and Sam went frantic, pulling his hand away from himself as fast as possible. A very bashful Winchester came out, soaked to the bone, in a white motel towel that was entirely too short for his tall frame. 

Dean's face was also red. It had been a long time since Sam had seen him this embarrassed. 

"Get on your own bed, Sasquatch." Dean commanded strongly, avoiding looking in Sam's direction entirely. 

"You mean the one you were just in?" Sam snarked. "In ladies underwear?" 

"Ha ha. Joke's over, now move your ass." Dean stood at the edge of the bed, one hand pinning the towel to the V of his waist, tan abs dripping wet. 

"Hell no, man! Probably jerked off on my sheets!" 

"You'll never know. What I do know is, I definitely jerked off in _those_ sheets last night." Dean pointed to his bed, a chuckle spreading to his face as he began a full belly laugh. 

Sam shot up which only made Dean laugh harder. 

"Gross, dude! Is there anything in this room you _haven't_ jerked off on?" 

"You, for starters." Dean laughed it off like a joke, running a second towel through his scruffy hair. 

"Hey, don't threaten me with a good time." Sam played along, but honestly having Dean naked for so long in such close proximity after what just happened? You could smack Sam's dick with a 2x4 and he would stay just as hard as he is now. 

Dean flopped down on the bed, idle hands running across his bare stomach while the other ran through his soft locks. 

"Why the tube top?" Sam was very serious, suddenly, curiosity taking over his filter. 

"Look, man-" 

"We don't have to talk about it if you don't want to. Curious, is all." 

"It's- uh- It's alright. I mean," Dean sat up and shifted his legs to the side of the bed, huffing a harsh breath. "I don't know, man. It's just somethin' I do. I know that makes me a freak or something-" 

"Don't, Dean. Don't do that to yourself. You're not a freak. You like what you like and that's that. Everyone has their... kinks." 

"You sound like you speak from experience." Dean smirked, his eyes wide and full of wonderment. 

"I do." Sam spread his legs and closed them again, willing his hardness to go away. Little did he know that Dean was watching, and the second that Dean saw Sam's abnormally large cock creeping down his leg like a ball python, he put two and two together. 

The sight of Dean in women's underwear had turned him on. and now he showed it physically more than anything else. 

"Do you- uh-" Dean sighed. Here goes. "Have weird kinks, Sammy?" 

"Anyone who says they don't have fantasies are all lying." 

"Stop avoiding the question, asshat. Do you?" Dean's gaze dropped to his fingers which were laced together tightly, trying not to fidget while he waited for an answer he wasn't sure if he was ready to hear. 

"It depends on what you consider odd, Dean." Sam carded his hands through his hair. It was getting longer and he kind of liked it. 

"You know. Something other than missionary and doggie." 

"Then I guess I do." Sam's cock throbbed, tenting his jeans more than he'd like as he imagined those positions with his older brother in those panties. Bent over the bed and looking back at him. 

"Since you uh-" Dean looked up at Sam and sighed. "You know one of mine, care sharing one with the class?" 

"Uh, no!" 

"Dude, come on. I practically taught you everything you know about sex! 'Member that one time at Gloria Gene's? 7 minutes in heaven with that one girl? What was her name?" 

"First off, _his_ name was Max. Secondly, that was you! I sat there and drank club soda while you made out with everyone in that room." 

"Oh, that's right. That was me." Dean's thoughts wandered to Max's tight ass and big cock. One he never got to experience. "You never answered me. Com'on, Sammy. I'm never out in the open like this. Let's go. Spill." 

"Alright, yeah. I'm into.. something like that." 

"Gonna tell me what it is, or am I gonna have to beat it out of you?" Dean was chuckling again, laugh lines dug in deep and his eyes sparkling like twilight. 

"Guess you're gonna have to beat it outta me!" Sam tucked his fingers behind his head and laid back on Dean's bed. 

Dean leaped over him, the crushing weight spread across his lap and while Dean was laughing over Sam, his stomach compressed and pushed out. Sam punched him in the ribs and tried to push him off. Dean squirmed and sat up, straddling Sam's lap and licked his finger. 

"I will so wet willy you!" 

"Will not!" Sam pushed his chest, but it didn't defer Dean. He moved quickly, sticking his finger in Sam's ear. 

"Fuck, dude! Stop!" Sam whined while laughing and Dean leaned over to lick Sam's cheek. Sam kept pushing, realizing that Dean was still just in a towel. Sam stopped moving, stopped breathing, stopped everything and when Dean noticed, he brought his head up a little. 

They were so close, they were breathing each other's air and Sam could smell the minty toothpaste Dean had used. Dean's eyelashes were a golden blonde, and they made his eyes light up. They sat for a moment, unmoving, not thinking. Dean dragged his tongue across his bottom lip and the shiny spit was mesmerizing. 

Sam leaned up and connected their lips. Dean was so warm and his soft lips were always the way Sam had imagined them. Dean melted into the kiss, letting out a soft "hmm" before he started pushing away. 

"What the hell?!?" Dean leapt off of Sam and his towel dropped. Dean bent to pick it up and scrambled to cover himself. Sam was mortified. Why had he done that? 

"Dude, the panties.. and the tube top.. I j-just..." Sam pressed his fingers into his eyes hoping Dean didn't notice the massive erection shooting up his pants. 

"That's what you're into?" Dean spread his arms defensively and the towel sagged a bit, he dropped one to retrieve it. 

"Maybe! I don't know!" 

"How do you not know? You are or you aren't!" 

"Alright, I am! Happy now, Dean?" 

"Yes!" Dean screamed. 

"Why are we still yelling!?" 

"I don't know!" 

Dean looked down and sat on the edge of the bed, huffing a deep breath as his muscles shifted into place. He could feel his body clicking like a rollercoaster going uphill, waiting for the descend. He thought about the kiss, Sam's situation, the way he reacted. Fuck it. Fuck it all. 

Dean jumped back on top of Sam and kissed him. Deep, hard, motionless. They were fluid in their movements, Dean licking Sam's lips asking for access and Sam let him in. Their tongues pressured each other, making the silky smooth saliva heated. Sam laid his hand of Dean's cheek, the other around his shoulders, pulling him in. Dean tasted so good. They were breathless as they pulled apart, only to be sucked back in by the look in each other's eyes. 

Dean ground his hips against Sam, feeling his throbbing harness against his skin. Sam reciprocated, bucking up into Dean. The eldest squirmed, bowing his head to suck on Sam's neck while he pulled the towel from his hips. He fumbled with Sam's button, his zipper fly, and Sam helped him pull his jeans down. Sam tossed his brother off to the other side of the bed, smirking silently. He tore his shirt open, chucking it to the side of the room. Sam stripped his boxers off quickly, his proud cock thumping with his heartbeat while he eyed Dean, sprawled on the bed. Dean pumped his own dick, watching, waiting, smearing the precome across the tip and down the shaft. Sam pulled off his wife beater and climbed back onto the bed. 

They knew this was wrong. With every hurt look and insecure touch, they knew. Somehow it didn't matter in this moment. 

Sam straddled his hips, and Dean offered a confused look. His broad shoulders and large frame shadowed his older brother as he bent over to take Dean's lips again. 

When they parted for breath, Dean began to litter kisses across Sam's pectoral muscles. 

"That thing I'm into?" Sam sat up and slotted Dean's cock between his ass, sweat slick and rubbing all the right places. Sam tore his head back in a moan and ground down, running the tip of Dean's dick against the rim of his entrance. "It has something to do with this." 

"With me?" Dean looked up into those burnt auburn eyes staring back at him. 

"God, yes." Sam licked his bottom lip and inhaled the scent of his brother on himself, bending to mouth at Dean's neck. He pushed slightly down, preparing his body for an intruding member. He felt himself give, let the feeling wash over him, the unpreparedness, the passionate selfishness, the unpredictable outcome. He pushed all his doubts, all his worries off, and just let himself have this. 

Dean nipped Sam's collarbone and placed his hands on Sam's cheeks, manipulating him to where he could kiss those lips again. Sam was sweet, like honey and wine and Dean couldn't stop himself. He let his hands roam wherever he wanted, finally, finally, feeling his back muscles, caressed his pulsating neck, grasped Sam's tight ass. When he had one asscheek in one hand, he felt them separate and slotted himself between them, pushing up. Sam moaned and slid down. 

Sam winced as Dean slid himself inside. Dean went even slower, watching his face for any signs of discomfort. When Sam briefly opened his eyes, he saw his brother's exquisite emerald eyes staring back and instantly smiled. 

"'M fine. 'S been a while." Sam's breath hitched and he let out a low pitched sigh, half of Dean's cock enveloped in Sam's tight heat and Sam couldn't wait until this part was over. With no prep and little to no time to adjust, this _**hurt**_ but it was so freakin' worth it. 

Dean was patient, a growl emerging from his throat as his balls touched Sam's flesh. He was all the way inside Sam, the object of his affection for years, all he's wanted, and this was happening. Dean sat, unmoving, with his head thrown back in a silent moan, breath hitching as Sam clenched and rocked his hips. 

Sam moved, forward and back, trying to acclimate as quickly as possible. He kissed Dean wholeheartedly, his mouth slack with an luscious groan as he pulled himself up for the first time. He made it halfway before pushing himself back down. Dean let out a deep hitched breath, moving his hands to Sam's hips. He gripped them tightly, feeling the knuckles of his fingers twitch. 

"Sammy-" Dean muttered for a lack of anything else to say. 

Sam was so tight around Dean it was almost a dream. Sam pulled himself up again, all the way this time, tight around Dean's head and Sam thrusted down quickly, eliciting another moan from Dean. Sam began to fuck quickly, his cock bouncing off of Dean's stomach until he moved his hand from Sam's hip and touched Sam's warm member for the first time. It was velvet smooth, pink as the blush and exertion on Sam's face. 

Dean didn't have to move, Sam's thrusting motion moved Dean's hand for him along his cock. The older Winchester tilted his head back along the headboard, the stimulation too much. Sam bowed to mouth at Dean's neck while Dean took over, bucking his hips up into Sam's tight heat while Sam sucked a bruise into his jugular. Sam moaned when his older brother glided across his prostate, hammering it on every inward thrust and Sam came, white spurts across Dean's chest as he hyperventilated. Dean was close, too soon, too much and Sam sat back and rode Dean like he was made to. 

He tilted his hips, picked himself up and dropped down again, Dean's fingernails digging into Sam's flesh and Dean began to pulsate inside him, coming shortly after. Dean's eyes rolled back into his head and he let out an aggressive groan, flexing his fingers to their full length. 

Sam laid his forehead against his older brother's for a moment, both huffing for air their lungs denied them, and just looked at each other. Sam admired Dean's glowing, wide eyes, his divine freckles dusted across his nose. Dean watched Sam's lax features, his long chestnut locks curling at the edges and Sam's kiss reddened lips pursed, his white teeth shining through. Sam's chest heaved, and sat up, a subtle squelch as Dean fell out of him. 

Sam sighed, not wanting to move, or speak, or do anything else other than be in his big brother's arms as long as he could. 

Dean exhaled shortly after and gripped his fingers back on Sam's hips. 

"Now what, Sammy?" 

Sam knew exactly what he meant. Now that they had crossed this line? Was it a momentary step forward or was this a lapse in judgement? Were they both yearning for this moment, or was it simply no chicks for too long? Sam observed Dean, watching Dean's eyelashes flutter and open, couldn't think of anything more perfect to say in that moment other than; 

"Now, you go put the panties back on and _I_ get to fuck _you._ " 

The smirk on Dean's face couldn't have been bigger. 

.END.


End file.
